A Guide Through Hugh Hefner Gorgeous Wives and Girlfriends

Latest update: Oct 03, 2017
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The most famous man among ladies, Hugh Hefner, died on Wednesday, Sept. 27, at the age of 91. When thinking about his numerous legacies, there are at least two things that come to mind. First of all, by founding Playboy, Hugh became a sexual revolution symbol who brought pornography into the mainstream. He was the first person who set the difference between the words "Sweetheart" and "Playmate.” The Playboy’s idea to sell pleasure and advocate variety instead of steady dates has made Hefner one of the transformative cultural figures in American life.

People who knew Hugh Hefner realized the broadness of his vision, mindset, and philosophy. He was not just selling nude photos; he was an expert at understanding brain, mind, and soul of his potential readers. He knew that men of his generation liked not only beautiful women but also were interested in politics, music, fashion, and art. Having that understood he did various interviews with famous and exciting people and deviated from the traditional role of husband and corporate drone.

Since 1949, Hugh Hefner has been married three times and has dated lots of beautiful Playboy bunnies. Although he claimed to have affairs with more than a 1000 women, not all of them were his actual girlfriends. While the most of his ladies are difficult to keep track of, here is a list of most prominent women who have played a major role in his life.

The Most Prominent Women in Hefner's Life

In 1949 Hugh Hefner Married His First Wife Mildred Williams

His first wife is probably one of the less known women from the hit-parade. Being his first college love, Mildred has given him two children, changed his views on sexuality, and shaped the major part of Hefner’s legacy. According to UK Daily Mail,
“his first sexual experience was with his first wife, Milly, whom he met while they were both in college.”
The couple stayed together until 1959, as Mildred admitted that she’d had an affair when Hugh was in the army.

Hugh has created Playboy while he was in relationships with Mildred. While he was serving in the Army, being a college student and getting certain experience in the magazine industry, he came up with the idea of founding men’s magazine. After borrowing money from his friends and family, Hefner created the first issue of Playboy in December 1953. And it became an immediate success.

From 1969 to 1976 Hugh Hefner dated his next girlfriend Barbara Lynn Klein who changed her name to Barbi Benton.

After the divorce, Hugh continued dating with Playboy models. His first big affair was with Playmate Benton. The couple lived together for seven years until they remained friends. Hugh Hefner eventually admitted that their split was one of his biggest mistakes.

Hugh Hefner dated Carrie Leigh for five years in the '80s before breaking up with her.

After living together for five years, Leigh has left the Playboy Mansion and filed several lawsuits against Hugh - one lawsuit was for publishing unauthorized photos of her. According to The Washington Post interview in 1999,
“It's almost like a cult. When you live in an environment like that that's so different from how other people live; you start forgetting who you are and what you believe is right.”
She added:
“It took me a few years after I did leave to wipe it out of my head."

Hefner married his second wife Kimberley Conrad when she was 26.

In 1989 the Playboy star married his next wife, Kimberley Conrad, who gave him two sons Marston and Cooper. Hugh and Kimberly broke up in 1998 until they officially separated 11 years later in 2010.

As he told People magazine in 2009,
"I would've been happy to divorce her when we separated, but she wanted to remain married for our boys."

Holly, Bridget, and Kendra have been the stars of the El’s TV show "The Girls Next Door," which debuted in 2005 and had six seasons to 2010. After they separated Hugh and Kendra stayed friends for many years. She married to a Philadelphia Eagles’ Hank Baskett and had two children.

Following the death of Hugh Hefner, Kendra released a statement mourning her ex-boyfriend,
“He made me the person I am today. I couldn't be more thankful for our friendship and our time together. I will miss him so much, but he will be in my heart forever.”

In 2010 Hugh became engaged to his third wife, a 24-year-old Crystal Harris.

Hefner proposed to Harris in December 2010, and in two years they got married. They happily lived until Hefner’s death. Since Hugh Hefner has died, Harris deleted her Instagram account and set her Twitter to private.

Although Hugh Hefner’s life and legacy are full of contradictions, he was undoubtedly one of the most prominent figures and cultural icons in journalism and the sexual revolution.

Elaine Chao is a senior writer for HookupGuru, covering the intersection of casual sex tips and tricks, intimacy, relationships and hookup dating. When it comes to finding an expert on casual sex, you can't come much closer than Elaine Chao.

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